JPS6315825A - Flame retardant for synthetic resin - Google Patents
Flame retardant for synthetic resinInfo
- Publication number
- JPS6315825A JPS6315825A JP15749486A JP15749486A JPS6315825A JP S6315825 A JPS6315825 A JP S6315825A JP 15749486 A JP15749486 A JP 15749486A JP 15749486 A JP15749486 A JP 15749486A JP S6315825 A JPS6315825 A JP S6315825A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- flame retardant
- formula
- general formula
- diglycidyl ether
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000003063 flame retardant Substances 0.000 title claims abstract description 34
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 229920003002 synthetic resin Polymers 0.000 title claims abstract description 17
- 239000000057 synthetic resin Substances 0.000 title claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- -1 ether compound Chemical class 0.000 claims abstract description 14
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 125000001118 alkylidene group Chemical group 0.000 claims abstract 5
- 125000005843 halogen group Chemical group 0.000 claims abstract 4
- 239000000126 substance Substances 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 239000004593 Epoxy Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- WHHGLZMJPXIBIX-UHFFFAOYSA-N decabromodiphenyl ether Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br WHHGLZMJPXIBIX-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 3
- 229910000410 antimony oxide Inorganic materials 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 238000009529 body temperature measurement Methods 0.000 description 2
- 150000002366 halogen compounds Chemical class 0.000 description 2
- 238000009863 impact test Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- QEZIKGQWAWNWIR-UHFFFAOYSA-N antimony(3+) antimony(5+) oxygen(2-) Chemical compound [O--].[O--].[O--].[O--].[Sb+3].[Sb+5] QEZIKGQWAWNWIR-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
Landscapes
- Polyethers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、合成樹脂な難燃化させるための難燃剤に関す
るものである。さらに詳しくは本難燃剤を配合した際、
機械的特性（特に耐衝撃性）、耐熱性、電気的特性、耐
水性、耐薬品性および成形加工性等に優れ、かつ優れた
難燃性を有する合成樹脂を提供する難燃剤に関するもの
である。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a flame retardant for making synthetic resin flame retardant. For more details, when this flame retardant is blended,
This relates to flame retardants that provide synthetic resins that have excellent mechanical properties (especially impact resistance), heat resistance, electrical properties, water resistance, chemical resistance, moldability, etc., and also have excellent flame retardancy. .
従来から合成樹脂用難燃剤としては、酸化アンチモンな
どの難燃助剤と併ｍ Ｌ／てハロゲン系化合物が使用さ
れている。このうち主なものとしては、テトラブロモビ
スフェノールＡ、デカブロモジフェニルオキシド、フ゛
ロム化ポリカーボネート、フ゛ロム化エポキシオリゴマ
ーなとがあけられるが、機械的特性、耐熱性、耐候ｔ！
１なとの諸物性の点で各々一長一短があった。Conventionally, halogen compounds have been used as flame retardants for synthetic resins in combination with flame retardant aids such as antimony oxide. Among these, the main ones are tetrabromobisphenol A, decabromodiphenyl oxide, fluorinated polycarbonate, and fluorinated epoxy oligomer, which have excellent mechanical properties, heat resistance, and weather resistance.
Each had advantages and disadvantages in terms of physical properties.
例えば、低分子量タイプ（デトラブロモビスフェノール
Ａ、デカブロモジフェニルオキシドなど）の添加型合成
樹脂用難燃剤を使用した成形物には、難燃剤のブリード
アウト、高温成形時の難燃剤による加熱着色、昇華等に
よる難燃効果の減少、耐候性の劣化といった欠点があっ
た。For example, molded products using additive type flame retardants for synthetic resins of low molecular weight type (detrabromobisphenol A, decabromodiphenyl oxide, etc.) may suffer from bleed-out of the flame retardant, heat coloring by the flame retardant during high-temperature molding, etc. There were drawbacks such as a decrease in flame retardant effect due to sublimation, etc., and deterioration in weather resistance.
一方、比較的高分子最タイプであるオリゴマー型難燃剤
では、低分子量タイプの難燃剤の欠点をある程度補い、
耐熱性、耐候性、電気的特性、耐水性、耐薬品性、成形
加工性等に優れた特性を示した。しかしながら、一般式
（ｍＶ）
（式中Ｘはハロゲン原子、ａ、ｂ、ｃ、ｄ、は１〜２の
整数、Ｒは炭素数１〜４のアルキリデン基またはアルキ
レン基、およびｌは０以上の整数を示す。）
であられされるエポキシオリゴマー型難燃剤では、機械
的強度の上で問題となる点も多く、例えば、ＡＢＳ樹脂
については、耐衝撃性の低下を起こす結果となった。ま
た上記の化合物（ｍＶ）の末端エポキシ基な一官能性フ
エノール類（例えばハロゲン化フェノールなど）で封鎖
した化合物についても、同様に耐衝撃性の改良は満足す
べきものではなかった。On the other hand, oligomer-type flame retardants, which are relatively the highest type of polymer, compensate to some extent for the disadvantages of low-molecular-weight flame retardants.
It exhibited excellent properties such as heat resistance, weather resistance, electrical properties, water resistance, chemical resistance, and moldability. However, the general formula (mV) (in the formula, The epoxy oligomer type flame retardant coated with (integer) has many problems in terms of mechanical strength, and for example, in the case of ABS resin, impact resistance has deteriorated. Similarly, the impact resistance of the above-mentioned compound (mV) blocked with a monofunctional phenol having an epoxy group (eg, halogenated phenol) was not satisfactory.
本発明者等は、以上のような従来の難燃剤りこ見られる
欠点を改良すべく鋭意検討した結果、耐熱性、耐候性、
電気的特性、耐水性、耐薬品性、成形加工性等に優れた
特徴を有し、しかも機械的特性（特に耐衝撃性）に優れ
た合成樹脂を提供するエポキシオリゴマー型難燃剤の開
発に剰った。As a result of intensive study to improve the drawbacks of conventional flame retardants as described above, the inventors of the present invention have found that they have improved heat resistance, weather resistance,
We are working hard to develop epoxy oligomer flame retardants that provide synthetic resins with excellent electrical properties, water resistance, chemical resistance, moldability, etc., as well as excellent mechanical properties (especially impact resistance). It was.
本発明による難燃剤は、ジグリシジルエーテル化合物（
ａ）１．０モルとジヒドロキシ化合物（ｂ）０．５〜１
．０モルを反応させることにより得られる。ここで得ら
れた難燃剤のハロゲン含有率は、少なくとも１０重重％
以」二必墾であり、４０重量％以上のものが好ましい。The flame retardant according to the present invention is a diglycidyl ether compound (
a) 1.0 mol and dihydroxy compound (b) 0.5-1
．． Obtained by reacting 0 mol. The halogen content of the flame retardant obtained here is at least 10% by weight.
The content is preferably 40% by weight or more.
本発明の難燃剤を合成する際のポイントは、一般式（、
Ｉ ）であられされるジグリシジルエーテル化合物を使
用することにある。一般式（１）のジグリシジルエーテ
ル化合物は、一般式（ｍ）のジヒドロキシ化合物に、ア
ルキレンオキシドを付加し、常法によりエポキシ化する
事で得られる。ここで、ジグリシジルエーテル化合物（
ａ）は、一般式（１，）の化合物を単独で使用しても、
一般式（ｎ）の化合物と併用してもかまわない。ただし
、一般式（ＩＩ）の化合物を併用する場合、ジグリシジ
ルエーテル化合物（ａ）は、一般式（１）の化合物が１
０重量％以以上型れていることが好ましい、また、一般
式（１）において、ｍ、ｎ）５の化合物を使用した場合
には、耐熱性などの面で不充分となる。The key points when synthesizing the flame retardant of the present invention are the general formula (,
The present invention consists in using diglycidyl ether compounds prepared by I). The diglycidyl ether compound of general formula (1) can be obtained by adding an alkylene oxide to the dihydroxy compound of general formula (m) and epoxidizing it by a conventional method. Here, diglycidyl ether compound (
a), even if the compound of general formula (1,) is used alone,
It may be used in combination with the compound of general formula (n). However, when the compound of general formula (II) is used in combination, the diglycidyl ether compound (a) is
It is preferable that the molding content is 0% by weight or more. Furthermore, if a compound of m, n) 5 in the general formula (1) is used, the heat resistance will be insufficient.
本発明による難燃剤を配合した合成樹脂は、優れた難燃
性を有し、耐熱性、耐候性、電気的特性、耐水性、耐薬
品性、成形加工性等の諸物性も優れ、かつまた優れた機
械的特性（特に耐衝撃性）を示すものとなる。The synthetic resin blended with the flame retardant according to the present invention has excellent flame retardancy, and also has excellent physical properties such as heat resistance, weather resistance, electrical properties, water resistance, chemical resistance, and moldability. It exhibits excellent mechanical properties (especially impact resistance).
本発明の合成樹脂用難燃剤の用途としては、ポリエチレ
ンテレフタレート、ポリブチレンテレフタレート等のポ
リエステル、ポリアミド、ポリカーボネート、ポリウレ
タン、ポリフェニレンエーテル、ポリエチレン、ポリプ
ロピレン、エチレン／酢酸ビニル共重合体、ポリフェニ
レンサルファイド、ポリスチレン、ＡＢＳなどの合成樹
脂があげられるが、なんらこれらに限られるわけでもな
く、特に耐衝撃性が要求される合成樹脂の難燃化に適し
ている。本発明の難燃剤の使用にあたっては、他の公知
の難燃剤（窒素系化合物、リン化合物、ハロゲン系化合
物）と４１１用してもよく、また、必要に応じて難燃助
剤（酸化アンチモン、酸化モリブデン、酸化スズなど）
として公知の化合物と併用してもよい。Applications of the flame retardant for synthetic resins of the present invention include polyesters such as polyethylene terephthalate and polybutylene terephthalate, polyamides, polycarbonates, polyurethanes, polyphenylene ethers, polyethylene, polypropylene, ethylene/vinyl acetate copolymers, polyphenylene sulfide, polystyrene, and ABS. Examples include, but are not limited to, synthetic resins such as, but are particularly suitable for making flame retardant synthetic resins that require impact resistance. When using the flame retardant of the present invention, it may be used with other known flame retardants (nitrogen compounds, phosphorus compounds, halogen compounds), and flame retardant aids (antimony oxide, antimony oxide, molybdenum oxide, tin oxide, etc.)
It may be used in combination with a compound known as .
以下に合成例及び実施例を挙げて本発明を具体的に説明
するが、本発明は、その要旨をこえないかぎり、以下に
しめず合成例及び実施例に制約されるものではない。The present invention will be specifically explained below with reference to synthesis examples and examples, but the present invention is not limited to the synthesis examples and examples as long as it does not go beyond the gist thereof.
合成例１
２．２−ビス（４−ヒドロキシエトキシ−３，５−ジブ
ロモフェニル）プロパンのジグリシジルエーテル（エポ
キシ当量４６３、以下１’ Ｂ Ａ Ｅ ＯＧＥと略す
）６００部、２．２−ビス（４−ヒドロキシ−３，５−
シフ゛ｉ二ｌモフェニル〉プロパンのジグリシジルエー
テル（エポキシ当量４００、以下ＴＢＡＧＥと略す）１
９３部及び２，２−ビス（４−ヒドロキシ−３，５−ジ
ブロモフェニル）プロパン（以下ＴＢＡと略す）２０６
部をフラスコにとり、トリエチルヘンシルアンモニウム
クロライド ０．１部を添加したのち、窒素気流下１５
０℃まで昇温し、６時間反応した。反応終了後、冷却、
粉砕し、淡黄色粉末の生成物を得た。この生成物は、エ
ポキシ当量１０２０、軟化点９２℃、臭素含有量４５．
１％であった。Synthesis Example 1 600 parts of diglycidyl ether of 2.2-bis(4-hydroxyethoxy-3,5-dibromophenyl)propane (epoxy equivalent: 463, hereinafter abbreviated as 1' BA E OGE), 2.2-bis( 4-hydroxy-3,5-
Diglycidyl ether of propane (epoxy equivalent: 400, hereinafter abbreviated as TBAGE) 1
93 parts and 2,2-bis(4-hydroxy-3,5-dibromophenyl)propane (hereinafter abbreviated as TBA) 206
After adding 0.1 part of triethylhensyl ammonium chloride to a flask, the mixture was heated for 15 minutes under a nitrogen stream.
The temperature was raised to 0°C and the reaction was carried out for 6 hours. After the reaction is complete, cool
The product was ground as a pale yellow powder. This product has an epoxy equivalent weight of 1020, a softening point of 92°C, and a bromine content of 45.
It was 1%.
合成例２
ＴＢＡＥＯＧＥ ７３６部、ＴＢＡ ２８５部をフラ
スコにとり、テトラメチルアンモニウムクロライド ｏ
、 １１１ｔｓを添加したのち、窒素気流下１５０℃
まで昇温し、５時間反応した。反応終了後、冷却、粉砕
し、淡黄色粉末の生成物を得た。Synthesis Example 2 736 parts of TBAEOGE and 285 parts of TBA were placed in a flask, and tetramethylammonium chloride o
, After adding 111ts, heat at 150℃ under nitrogen stream.
and reacted for 5 hours. After the reaction was completed, the mixture was cooled and pulverized to obtain a pale yellow powder product.
この生成物は、エポキシ当量２０３０、軟化点９５℃、
臭素含有量 ４４．９％であった。This product has an epoxy equivalent weight of 2030, a softening point of 95°C,
Bromine content was 44.9%.
合成例３
２．２−ビス［４−（２−ヒドロキシプロポキシ）−３
，５−ジブロモフェニル］プロパンのジグリシジルエー
テル（エポキシ当量５０２）６５０部、ＴＢＡＧＥ
１９３部及びＴＢＡ ２０６部をフラスコにとり、ト
リエチルベンジルアンモニウムクロライド ０．１部を
添加したのち、窒素気流下１５０℃まで昇温し、６時間
反応した。反応終了後、冷却、粉砕し、淡黄色粉末の生
成物を得た。Synthesis Example 3 2.2-bis[4-(2-hydroxypropoxy)-3
,5-dibromophenyl]propane diglycidyl ether (epoxy equivalent weight 502) 650 parts, TBAGE
After 193 parts and 206 parts of TBA were placed in a flask and 0.1 part of triethylbenzylammonium chloride was added, the temperature was raised to 150° C. under a nitrogen stream and reacted for 6 hours. After the reaction was completed, the mixture was cooled and pulverized to obtain a pale yellow powder product.
この生成物は、エポキシ当量１０３０．軟化点９２℃、
臭素含有量４４．２％であった。This product has an epoxy equivalent weight of 1030. Softening point 92℃,
The bromine content was 44.2%.
次に、比較のため、一般のエポキシオリゴマー型難燃剤
の合成を、以下のとおり行った。Next, for comparison, a general epoxy oligomer type flame retardant was synthesized as follows.
合成例４
ＴＢＡＧＥ ７５０部、ＴＤＡ ２４０部をフラス
コにとり、トリエチルベンジルアンモニウムクロライド
０．１部を添加したのち、窒素気流下１５０℃まで昇
温し、５時間反応した０反応終了後、冷却、粉砕し、淡
黄色粉末の生成物を得た。Synthesis Example 4 750 parts of TBAGE and 240 parts of TDA were placed in a flask, and 0.1 part of triethylbenzylammonium chloride was added thereto.Then, the temperature was raised to 150°C under a nitrogen stream, and the mixture was reacted for 5 hours. After the completion of the reaction, it was cooled and pulverized. , the product was obtained as a pale yellow powder.
この生成物は、エポキシ当量１ｏｌｏ、軟化点１３２℃
、臭素含有量 ６１．４％であった。This product has an epoxy equivalent of 1olo and a softening point of 132°C.
, the bromine content was 61.4%.
実施例１〜３
ＡＢＳ樹脂 １００重量部、合成例１〜３の化合物 ２
０重量部、二酸化アンチモン ５重量部を混合し、押出
様にてペレタイズし、射出成形機にてそれぞれＵＬ−９
４燃焼試験、アイゾツト衝撃試験、引張試験、耐候性試
験、熱変形温度測定の試験片を成形し、各試験を行った
結果を表−１に示した。Examples 1-3 ABS resin 100 parts by weight, compounds of Synthesis Examples 1-3 2
0 parts by weight and 5 parts by weight of antimony dioxide were mixed, pelletized by extrusion, and molded into UL-9 by an injection molding machine.
4. Test pieces were molded for a combustion test, an Izod impact test, a tensile test, a weather resistance test, and a heat distortion temperature measurement, and the results of each test are shown in Table 1.
比較例１〜３
実施例１〜３と同様に合成例４の化合物、ＴＢＡ、デカ
ブロモジフェニルオキシド（以下ＤＢＤＰＯと略す）を
配合して試験片を成形し、各試験を行った結果を表−１
に示した。Comparative Examples 1 to 3 In the same manner as Examples 1 to 3, the compound of Synthesis Example 4, TBA, and decabromodiphenyl oxide (hereinafter abbreviated as DBDPO) were blended to form test pieces, and the results of each test are shown in Table 1. 1
It was shown to.
各試験方法
難燃性試験はＵＬ−９４、アイゾツト衝撃試験はＪＩＳ
Ｋ７１１０（Ｖノツチつき）、引張強度試験はＪＩ
Ｓ Ｋ７１１３、熱変形温度測定（１８，６ｋｇ／（
２）２）はＪＩＳ Ｋ７２０７、耐候性試験はＪＩＳ
Ｋ７１０２に準じて行なった。Each test method Flame retardancy test is UL-94, Izod impact test is JIS
K7110 (with V notch), tensile strength test is JI
S K7113, heat distortion temperature measurement (18,6kg/(
2) 2) is JIS K7207, weather resistance test is JIS
It was carried out according to K7102.
また熱安定性試験は、各難燃剤５ｇを直径３７−のアル
ミカップにとり、２５０℃、３０分間加麹後の外観を判
断し
〇−変化なし、八−やや着色、Ｘ−著しく着色の３段階
で評価した。In addition, in the thermal stability test, 5 g of each flame retardant was placed in an aluminum cup with a diameter of 37 mm, and the appearance was judged after being malted at 250 ° C for 30 minutes. It was evaluated by
１ ！
以上の結果のごとく、本発明にかかる合成樹脂用難燃剤
は、すぐれた難燃性を付与するとともに、すぐれた熱安
定性、耐候性を持ち、機械的強度（特に耐衝撃性）を低
下させることが少ない。1! As shown in the above results, the flame retardant for synthetic resins according to the present invention not only provides excellent flame retardancy, but also has excellent thermal stability and weather resistance, and reduces mechanical strength (especially impact resistance). There aren't many things.
Claims (4)
、ジヒドロキシ化合物（ｂ）０．５〜１．０モルを反応
させて得られる生成物であって、ハロゲン含有率が１０
重量％以上の合成樹脂用難燃剤。(1) A product obtained by reacting 0.5 to 1.0 mol of a dihydroxy compound (b) with 1 mol of a diglycidyl ether compound (a), the product having a halogen content of 10
Flame retardant for synthetic resins in weight percent or more.
I ）及び一般式（II） ▲数式、化学式、表等があります▼（ I ） （式中Ｘはハロゲン原子、ｐ、ｑは０〜２の整数、Ｒ１
は炭素数１〜４のアルキリデン基、アルキレン基または
−ＳＯ＿２−基、Ｒ＿２はアルキレン基、ｍ、ｎは１〜
５の整数を示す。） ▲数式、化学式、表等があります▼（II） （式中Ｘはハロゲン原子、ｒ、ｓは０〜２の整数、Ｒ＿
３は炭素数１〜４のアルキリデン基、アルキレン基また
は−ＳＯ＿２−基を示す。） であらわされる特許請求の範囲第１項記載の合成樹脂用
難燃剤。(2) The diglycidyl ether compound (a) has the general formula (
I) and general formula (II) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, X is a halogen atom, p and q are integers from 0 to 2, R1
is an alkylidene group having 1 to 4 carbon atoms, an alkylene group or a -SO_2- group, R_2 is an alkylene group, m and n are 1 to
Indicates an integer of 5. ) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) (In the formula, X is a halogen atom, r and s are integers from 0 to 2, R_
3 represents an alkylidene group, an alkylene group, or a -SO_2- group having 1 to 4 carbon atoms. ) A flame retardant for synthetic resins according to claim 1.
I ）の化合物を単独、もしくは一般式（ I ）と一般式
（II）の化合物を併用して使用することを特徴とする特
許請求の範囲第１項または第２項記載の合成樹脂用難燃
剤。(3) The diglycidyl ether compound (a) has the general formula (
The flame retardant for synthetic resins according to claim 1 or 2, characterized in that the compound represented by I) is used alone or in combination with the compounds represented by general formula (I) and general formula (II). .
数式、化学式、表等があります▼（III） （式中Ｘはハロゲン原子、ｔ、ｕは０〜２の整数、Ｒ＿
４は炭素数１〜４のアルキリデン基、アルキレン基また
は−ＳＯ＿２−基を示す。） であらわされる特許請求の範囲第１項記載の合成樹脂用
難燃剤。(4) The dihydroxy compound (b) has the general formula (III)▲
There are mathematical formulas, chemical formulas, tables, etc.▼(III) (In the formula, X is a halogen atom, t and u are integers from 0 to 2, R_
4 represents an alkylidene group, alkylene group or -SO_2- group having 1 to 4 carbon atoms. ) A flame retardant for synthetic resins according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15749486A JPS6315825A (en) | 1986-07-04 | 1986-07-04 | Flame retardant for synthetic resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15749486A JPS6315825A (en) | 1986-07-04 | 1986-07-04 | Flame retardant for synthetic resin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6315825A true JPS6315825A (en) | 1988-01-22 |
Family
ID=15650910
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15749486A Pending JPS6315825A (en) | 1986-07-04 | 1986-07-04 | Flame retardant for synthetic resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6315825A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160091272A (en) * | 2015-01-23 | 2016-08-02 | 리브에르-베르잔테크니크 게엠베하 | Method and apparatus for the gear manufacturing machining of a workpiece by a diagonal generating method |
| KR20160091274A (en) * | 2015-01-23 | 2016-08-02 | 리브에르-베르잔테크니크 게엠베하 | Method for the gear manufacturing machining of a workpiece by a diagonal generating method |
| KR20230135028A (en) * | 2015-01-23 | 2023-09-22 | 리브에르-베르잔테크니크 게엠베하 | Method and apparatus for the gear manufacturing machining of a workpiece by a diagonal generating method |
-
1986
- 1986-07-04 JP JP15749486A patent/JPS6315825A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160091272A (en) * | 2015-01-23 | 2016-08-02 | 리브에르-베르잔테크니크 게엠베하 | Method and apparatus for the gear manufacturing machining of a workpiece by a diagonal generating method |
| KR20160091274A (en) * | 2015-01-23 | 2016-08-02 | 리브에르-베르잔테크니크 게엠베하 | Method for the gear manufacturing machining of a workpiece by a diagonal generating method |
| KR20230135028A (en) * | 2015-01-23 | 2023-09-22 | 리브에르-베르잔테크니크 게엠베하 | Method and apparatus for the gear manufacturing machining of a workpiece by a diagonal generating method |
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